Hydrochloric Acid → (E)-5-methyl-4-bis(4-fluorophenyl)methylidene-2-hexenoic acid

HRID 2380642ノート

反応式

HRID 2380642 の反応式
[CH3:1][CH:2]([CH3:26])[C:3](=[C:11]([C:19]1[CH:24]=[CH:23][C:22]([F:25])=[CH:21][CH:20]=1)[C:12]1[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=1)/[CH:4]=[CH:5]/[C:6]([O:8]CC)=[O:7].[OH-].[Na+].Cl>C1(C)C=CC=CC=1>[CH3:1][CH:2]([CH3:26])[C:3](=[C:11]([C:12]1[CH:13]=[CH:14][C:15]([F:18])=[CH:16][CH:17]=1)[C:19]1[CH:24]=[CH:23][C:22]([F:25])=[CH:21][CH:20]=1)/[CH:4]=[CH:5]/[C:6]([OH:8])=[O:7]

参加物

5

反応物 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 86747465HCID 86747465、化合物

生成物 1

HCID 18954766(E)-5-methyl-4-bis(4-fluorophenyl)methylidene-2-hexenoic acid収率 78%

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

反応条件

温度
60 °C

実験手順

A toluene (8 ml) solution of the above ester (2.38 g, 6.7 mmol) was added to powdery sodium hydroxide (0.34 g, 8.5 mmol) under argon atmosphere, and the whole was stirred at 60° C. for 5 hours. The reaction mixture was neutralized with 1M hydrochloric acid (10 ml) and extracted with ethyl acetate (25 ml×3 times). The organic layer was washed with water, saturated sodium chloride aq solution and then dried over anhydrous magnesium sulfate. Concentration of the organic layer in vacuo followed by recrystallization from a mixed solvent (hexane:ethyl acetate=4:1) gave 1.70 g (78% yield) of (E)-5-methyl-4-bis(4-fluorophenyl)methylidene-2-hexenoic acid. mp=225°-230° C. Rf =0.52 (hexane:ethyl acetate=1:1) IR (KBr): 3350, 2400, 3025, 1690, 1615, 1515, 1430, 1320, 1225, 1165, 1100, 1080, 1005, 965, 860, 850, 595, 580 cm-1.

後処理

  1. extractionextracted with ethyl acetate (25 ml×3 times)
  2. washThe organic layer was washed with water, saturated sodium chloride aq solution
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customConcentration of the organic layer in vacuo followed by recrystallization from a mixed solvent (hexane:ethyl acetate=4:1)

出典と根拠

ORDレコード
ord-5b5687f8450141daa202ed89c2bd0268
出典データセット
uspto-grants-1994_11
特許番号
US05369109

反応ノート

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